(R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

Base Information

• Chemical Name: (R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole
• CAS No.: 209682-64-4
• Molecular Formula: C16H22N2
• Molecular Weight: 242.36
• UNII: 68TX8Z5QGM
• Pharos Ligand ID: 9L69LTK8WWR2
• ChEMBL ID: CHEMBL45929
• Mol file: 209682-64-4.mol

Synonyms:209682-64-4;Eletriptan impurity F;68TX8Z5QGM;CHEMBL45929;5-ethyl-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole;(R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole;5-Ethyl-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-indole;1H-Indole, 5-ethyl-3-(((2R)-1-methyl-2-pyrrolidinyl)methyl)-;5-ethyl-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole;UNII-68TX8Z5QGM;SCHEMBL8507160;XQBUOODGXPTQOQ-CQSZACIVSA-N;BDBM50090522;5-Ethyl-3-((R)-1-methyl-pyrrolidin-2-ylmethyl)-1H-indole

Chemical Property of (R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 242.178298710
• Heavy Atom Count: 18
• Complexity: 278

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

5-Ethyl-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=CC2=C(C=C1)NC=C2CC3CCCN3C
• Isomeric SMILES: CCC1=CC2=C(C=C1)NC=C2C[C@H]3CCCN3C
• Uses: 5-Ethyl-3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-1H-indole is an impurity of Eletriptan (E505000), a serotonin 5-HTIB/ID receptor agonist and an antimigraine agent.

Technology Process of (R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

There total 15 articles about (R)-5-Ethyl-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.54%

(R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole (180637-89-2) → 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole (209682-64-4) + eletriptan (143322-58-1)

Guidance literature:

With methanesulfonic acid; 5%-palladium/activated carbon; hydrogen; In water; acetone; at 25 - 30 ℃;

DOI:10.1021/op3002454

Reference yield: 84.0%

(R)-5-(2-Benzenesulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole → eletriptan (143322-58-1) + (R)-3-[(1-methyl-2-pyrrolidinyl)-methyl]-5-ethyl-1H-indole (209682-64-4)

Guidance literature:

With hydrogen; In methanol; toluene; at 80 ℃; for 0.5h; under 3750.38 Torr; Temperature; Pressure; Overall yield = 84 percent; Inert atmosphere; Schlenk technique; Autoclave;

DOI:10.1007/s10562-020-03407-5

Reference yield:

(R)-5-bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole (143322-57-0,208464-41-9,312949-16-9) → 5-ethyl-3-{[1-methylpyrrolidin-2-yl]methyl}-1H-indole (209682-64-4) + eletriptan (143322-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; dmap / toluene / 0.25 h

2: tris-(o-tolyl)phosphine; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 0.25 h / 25 - 120 °C

3: sodium hydrogencarbonate / methanol; water / 40 - 50 °C

4: methanesulfonic acid; 5%-palladium/activated carbon; hydrogen / water; acetone / 25 - 30 °C

With dmap; methanesulfonic acid; 5%-palladium/activated carbon; hydrogen; palladium diacetate; sodium hydrogencarbonate; triethylamine; tris-(o-tolyl)phosphine; In methanol; water; N,N-dimethyl-formamide; acetone; toluene; 2: |Heck Reaction;

DOI:10.1021/op3002454

upstream raw materials:

5-ethyl-1H-indole

(R)-5-bromo-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole

PVS

(R)-1-acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Refernces

• 1、 Madasu, Suri Babu,Vekariya, Nagaji Ambabhai,Hari Kiran,Gupta, Badarinadh,Islam, Aminul,Douglas, Paul S.,Babu, Korupolu Raghu. "Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide". supporting information. p. 1400 - 1405. Retrieved 2012/11/07.
• 2、 Slassi, Abdelmalik,Edwards, Louise,O'Brien, Anne,Meng, Charles Q.,Xin, Tao,Seto, Caroline,Lee, David K.H.,MacLean, Neil,Hynd, Donna,Chen, Cora,Wang, Hong,Kamboj, Rajender,Rakhit, Suman. "5-Alkyltryptamine derivatives as highly selective and potent 5-HT(1D) receptor agonists". . p. 1707 - 1709. Retrieved 2007/10/03.